Hydrochloric Acid → HCID 54675515, compound

HRID 1850324Notes

Reaction equation

HRID 1850324 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([N:21]3[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1.Cl.C(OCC)C>>[N:21]1([C:16]2[C:15]([CH:13]3[CH2:12][N:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH2:14]3)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58546787HCID 58546787, compound

Product 1

HCID 54675515HCID 54675515, compoundYield 87%

Procedure

To a round bottomed flask was added tert-butyl 4-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)-1,4-diazepane-1-carboxylate (0.5340 g, 1.159 mmol, SCHEME 6, Example 6.15) and HCl, (1.0 M solution in diethyl ether (1.159 ml, 1.159 mmol)) and the reaction was allowed to stir at RT. After 1 h, the reaction mixture was concentrated, then diluted with saturated Na2CO3 and extracted with CH2Cl2. The organic extract was washed with saturated Na2CO3, saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo to give 2-(3-(3-(1,4-diazepan-1-yl)pyrazin-2-yl)azetidin-1-yl)quinoline (0.3627 g, 1.006 mmol, 87% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with saturated Na2CO3
  3. extractionextracted with CH2Cl2
  4. extractionThe organic extract
  5. washwas washed with saturated Na2CO3, saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac19bdd79f0a4b19bd2969a6cdffbd5a
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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